Ruthenium/Imidazolylphosphine Catalysis: Hydrogenation of Aliphatic and Aromatic Nitriles to Form Amines
A convenient and efficient catalyst system for the hydrogenation of aliphatic nitriles towards the corresponding primary amines in high to excellent yields is presented. In addition, aromatic nitriles are reduced smoothly, too. The use of low catalyst loadings and molecular hydrogen make this protoc...
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| Published in | Chemistry : a European journal Vol. 20; no. 15; pp. 4227 - 4231 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
07.04.2014
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
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| Abstract | A convenient and efficient catalyst system for the hydrogenation of aliphatic nitriles towards the corresponding primary amines in high to excellent yields is presented. In addition, aromatic nitriles are reduced smoothly, too. The use of low catalyst loadings and molecular hydrogen make this protocol an attractive methodology.
It's not complicated: A general and easy homogeneous catalyst system based on [Ru(cod)(methylallyl)2] and a cyclohexyl‐substituted imidazolylphosphine ligand for selective hydrogenation of aliphatic nitriles is presented. In addition, by using an isopropyl‐substituted imidazolylphosphine ligand, selected aromatic nitriles were reduced with excellent yields towards the primary amine. Furthermore, two new crystal structures give an insight of possible pre‐catalysts. |
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| AbstractList | A convenient and efficient catalyst system for the hydrogenation of aliphatic nitriles towards the corresponding primary amines in high to excellent yields is presented. In addition, aromatic nitriles are reduced smoothly, too. The use of low catalyst loadings and molecular hydrogen make this protocol an attractive methodology.
It's not complicated: A general and easy homogeneous catalyst system based on [Ru(cod)(methylallyl)2] and a cyclohexyl‐substituted imidazolylphosphine ligand for selective hydrogenation of aliphatic nitriles is presented. In addition, by using an isopropyl‐substituted imidazolylphosphine ligand, selected aromatic nitriles were reduced with excellent yields towards the primary amine. Furthermore, two new crystal structures give an insight of possible pre‐catalysts. A convenient and efficient catalyst system for the hydrogenation of aliphatic nitriles towards the corresponding primary amines in high to excellent yields is presented. In addition, aromatic nitriles are reduced smoothly, too. The use of low catalyst loadings and molecular hydrogen make this protocol an attractive methodology. Abstract A convenient and efficient catalyst system for the hydrogenation of aliphatic nitriles towards the corresponding primary amines in high to excellent yields is presented. In addition, aromatic nitriles are reduced smoothly, too. The use of low catalyst loadings and molecular hydrogen make this protocol an attractive methodology. A convenient and efficient catalyst system for the hydrogenation of aliphatic nitriles towards the corresponding primary amines in high to excellent yields is presented. In addition, aromatic nitriles are reduced smoothly, too. The use of low catalyst loadings and molecular hydrogen make this protocol an attractive methodology. It's not complicated: A general and easy homogeneous catalyst system based on [Ru(cod)(methylallyl) sub(2)] and a cyclohexyl-substituted imidazolylphosphine ligand for selective hydrogenation of aliphatic nitriles is presented. In addition, by using an isopropyl-substituted imidazolylphosphine ligand, selected aromatic nitriles were reduced with excellent yields towards the primary amine. Furthermore, two new crystal structures give an insight of possible pre-catalysts. A convenient and efficient catalyst system for the hydrogenation of aliphatic nitriles towards the corresponding primary amines in high to excellent yields is presented. In addition, aromatic nitriles are reduced smoothly, too. The use of low catalyst loadings and molecular hydrogen make this protocol an attractive methodology. [PUBLICATION ABSTRACT] |
| Author | Beller, Matthias Wendt, Bianca Jiao, Haijun Werkmeister, Svenja Spannenberg, Anke Bornschein, Christoph Junge, Kathrin |
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| Keywords | SELECTIVE HYDROAMINOMETHYLATION CARBOXYLIC-ACID ESTERS COMPLEXES HYDROAMINATION hydrogenation P ruthenium ALKENES N ligands ATOMS LI REDUCTION LIGANDS ENANTIOSELECTIVE HYDROGENATION nitrile amine GAUSSIAN-BASIS SETS P,N ligands |
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| Snippet | A convenient and efficient catalyst system for the hydrogenation of aliphatic nitriles towards the corresponding primary amines in high to excellent yields is... Abstract A convenient and efficient catalyst system for the hydrogenation of aliphatic nitriles towards the corresponding primary amines in high to excellent... |
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| SubjectTerms | Aliphatic compounds amine Amines Amines - chemistry Catalysis Catalysts Chemistry Chemistry, Multidisciplinary Coordination Complexes - chemistry Crystal structure Crystallography, X-Ray Hydrogenation Imidazoles - chemistry Ligands Molecular Conformation N ligands nitrile Nitriles Nitriles - chemistry P,N ligands Phosphines - chemistry Physical Sciences Ruthenium Ruthenium - chemistry Science & Technology |
| Title | Ruthenium/Imidazolylphosphine Catalysis: Hydrogenation of Aliphatic and Aromatic Nitriles to Form Amines |
| URI | https://api.istex.fr/ark:/67375/WNG-HSNR1ZZS-T/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.201303989 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000333632800005 https://www.ncbi.nlm.nih.gov/pubmed/24615766 https://www.proquest.com/docview/1512170330/abstract/ https://search.proquest.com/docview/1513050762 https://search.proquest.com/docview/1778009021 |
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